


Pregaming

by Deansrainbowslinky



Category: Supernatural
Genre: Alternate Universe - College/University, Anal Fingering, Blow Jobs, Cas is a porn star, Cigarettes, College Student Dean, Come Swallowing, Come in Underwear, Dirty Talk, Dom Castiel, Human Castiel, Humiliation, M/M, Masturbation, Mutual Masturbation, Panic Attacks, Porn Watching, Repressed Dean, Smut, Tutor Castiel, Tutoring, Underage Drinking, Voyeurism, Wet Dream, Work In Progress
Language: English
Status: In-Progress
Published: 2015-11-07
Updated: 2015-12-11
Packaged: 2018-04-30 11:58:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 12,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5163008
Author URL: https://archiveofourown.org/users/Deansrainbowslinky/pseuds/Deansrainbowslinky
Summary: <blockquote class="userstuff">
              <p>Dean needs a tutor to help him through his heavy workload at college.<br/>Castiel helps him.</p><p>Castiel needs to make extra money, and works his way through school.<br/>Dean is shocked to find Castiel on the internet..</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I have recently become obsessed with this AU..
> 
> Comments are very appreciated :D

Dean wasn’t sure how he even got into a college. During high school, it seemed like he missed more days than he was even present for his classes. He sucked at math, which he had to take again in summer school to even be eligible for a community college. Yet somehow, he made it. Sure, he needed to be tutored at least three days a week, but he was managing. 

After the first few weeks of the semester had started, he was finding his workload to be way too overwhelming. When he had imagined his college career, he pictured himself getting wasted at huge keggers, making tons of friends, and having lots of anonymous sex. In reality, he was having a really hard time making friends, never mind being invited to parties. There simply was not enough time to balance his schoolwork with any extracurricular activities. He had to constantly consider his ideal future to keep himself going. Sure, working as a mechanic for his uncle Bobby had proved to be a profitable experience, but there was no way in hell he was going to spend the rest of his life in a graveyard of shitty cars getting his hands dirty every day.

Trudging up the front stairs of the campus’ library, about 50 lbs of textbooks weighing him down in the backpack slung over his shoulder, he shook these thoughts off. It was time for his 4th tutoring session of the week, and he was not about to slack off and earn himself a fifth one.

He nudged open the door to the library’s “quiet area” to scope out his tutor amongst the endless rows of stressed out students studying in their cubicles. There he was, stationed by the windows at the far end, looking frazzled and sleepless. As Dean got closer, he caught sight of the OCD table space his tutor had set up, notebooks and pencils set up in a perfect line.

“Hello, Dean.” His tutor, Castiel, peered up over his glasses, greeting him with smiling blue eyes and a deep gravelly voice. 

Dean cleared his throat and threw his heavy sack of books down on the carpeted floor. “Hey there Cas.”

Castiel ran a hand through his already disheveled black mess of hair. “Please, call me Castiel.”

“Oh, sorry. Castiel.” Dean corrected himself in a sarcastic mocking voice.

He glared up at Dean for a second, and crossed his arms across his chest. “Please, sit.”

Dragging the heavy wooden chair out from its place under the table, Dean threw himself down onto it. He had to bite back a smile as he looked up, making eye contact with those shining blue eyes he refused to enjoy gazing at. Sure, this guy was cute as hell, but Dean would never let anyone know he recognized that. He was manly. He was rugged. He surely was not gay, not even a little bit. However, every time he spent his study sessions with Castiel, he had to fight the sexually conflicted bombardment of thoughts in his head. But fuck that, he was here to learn. 

“Okay,” Castiel began, adjusting his thick-rimmed glasses on the bridge of his nose. “Which section of today’s assignment is the most challenging to you, we can start there.”

Dean sighed, and hefted his trigonometry text book on to the table. “Kind of the whole thing?” He gave a nervous smile.

 

As their hour long session drew to a close, Dean was still absolutely lost, but was most disappointed in the fact that their time together was up. Maybe he would have picked up on more of what Castiel was trying to teach him if he could have focused on anything but his deep monotonous tone for even a second. It just.. did things to Dean. He didn’t know why he found it so hot, but decided it was in his best interest to completely ignore the thought process. 

“I will see you next Monday.” Castiel hurriedly packed his notebooks and pencils into his messenger bag. 

It sent a strange and disappointed feeling to Dean’s gut seeing Castiel scramble so quickly to get away from him. “Wait, uh. Cas?”

Castiel’s eyes bore into Dean. Shit, he had called him Cas again. Why did he keep doing that? They weren’t even friends. 

“What do you do for fun on weekends?” Dean threw on a sheepish grin and pretended that he wasn’t personally curious, just trying to find an invite to a party.

Eyes darting nervously around the room, Cas responded. “I party. You know, with my friends. We get.. drunk. Do fun things.” He tried hard to keep a cocky tone, maybe he could convince someone he wasn’t a loser for once. In reality, he mostly just went back to his dorm room to watch Netflix, enjoying the absence of his roommate, who was always out partying. A few weekends a month he would work, but that was not a conversation he was ready to have with anyone.

Dean tried his hardest to play it cool. “Yeah! Me too. Where do you usually party? I haven’t- I don’t know what to do tonight?”

Oh shit. It was evident in Dean’s rejected eyes that he was, in fact, a loser too. This revelation was somewhat comforting to Castiel. Dean acted like he was the coolest guy on campus, but come to think of it, when Castiel had seen him walking between classes, he was always alone in the swarm of students. 

“Off campus,” was Castiel’s cop out answer.  
***

Dean stopped at a convenience store on the way home to buy a fifth of whiskey. He had flirted his way into not showing an ID at the beginning of the semester, so buying booze wasn’t an issue.

The blonde girl behind the counter swept her long hair over her shoulder flirtatiously as he approached. “Third time this week, that’ll be $13.99, Mr. Popular.” She chuckled to herself and shot him a seductive look through her long eyelashes.

“Oh, you know it.” Dean smirked at her, offering a wink. He was never going to need to show an ID again. He rummaged through his pockets and pulled out a few crumpled up bills. 

He made his way back to the dorm, fifth of whiskey already open and taking gulps out of the paper bag. Oh yeah, he was Mr. Popular alright. Stumbling the last couple blocks to his dorm, Dean gazed up at the tall brick buildings surrounding him. Loud, thumping bass rattled the windows of one of the apartments, drunk students already lined up at the door to get in. He embarrassedly avoided eye contact and swerved out of their way into the street. Eyes still on the ground, Dean hopped up the curb back onto the cracked concrete sidewalk, and collided with a warm solid mass. 

“Oh, shit! I’m sorry.” Dean slurred, continuing to walk. A few strides past, a steady hand gripped at his bicep, and he whirled around. He was not in the mood to fight someone.

His glazed eyes locked on the stranger who was still grasping at his arm. Oh no.

“Dean. Where are you headed?” Castiel was still wearing his khakis and buttoned up cardigan, crisp collared shirt peeking out the top. 

“I, uh-” Dean fumbled with the fifth, trying to hind it behind his back.

Castiel’s eyebrows furrowed in concern. “Are you drunk? Where are your friends?”

He ripped his arm out of Castiel’s grip. “I’m fine Cas. Just doin’ some pregaming.” The most pathetic attempt at a smile tugged at the corners of Dean’s mouth.

“Okay.” Castiel was not buying it. “Have a good weekend, Dean. I will see you monday.”

At that, Dean took another huge swig of whiskey. How embarrassing. Now Castiel was gonna think he was an alcoholic. A lonely alcoholic. Drinking out of a goddamned paper bag on the sidewalk. Great.

Fifth of whiskey already halfway gone, Dean burst through the door of his dorm room, unintentionally slamming it shut behind him. Ambling over to the lamp next to his bed, he pulled the string and the bright light stung his sensitive eyes. He walked over to his desk to grab his laptop, and tripped over a shoe onto his bed. This was a new low for him. Already ashamed at the thought of getting hammered alone, he figured he’d just keep digging the hole deeper, and pulled up his internet browser. 

A pop up ad assaulted his eyes, two dudes on a couch getting each other off. The image should have repulsed him, he was straight after all. But it didn’t. Five minutes later he was propped up against his headboard, pants down, and 3 minutes into a gay porn video. He stroked in time with the black-haired guy on the screen, eyes scanning over his pale toned body, and pretending he hadn’t specifically searched for guys resembling Castiel. Once the video was over, he returned to the home screen, scrolling down the list of thumbnails trying to scope out a new Cas lookalike. 

It was just then that he heard his phone chime in the pocket of his jacket, which he had chucked across the room. He did the walk of shame, pants and boxers at his ankles, waddling across the room to recover it. The screen showed a little flashing blue envelope and read “1 New Message- Cas”. Fuck. He clicked it, wondering what the hell Castiel would want from him right now and scanned his eyes over the text bubble. “Hope you made it back safe. I am here for you if you ever need to talk.”

Great. Now Castiel knew he was a sad, lonely alcoholic with no friends. Worst of all, he had pegged him as a troubled type with so many issues that he needed a fucking therapist or something. To add to the list of things he probably needed therapy for was searching for pornos that starred guys who reminded him of his tutor. Still, it was a nice gesture, but Dean didn’t know what it felt like to be cared about. Inhibitions obliterated, Dean drunkenly replied. “Yeha man sall good. THinking about u”

As soon as Dean hit ‘send’ the horrifying reality of what just happened struck Dean. Oh shit. Shit fucking god dammit fuck. What had he just done? Cas was going to think he was creepy. Beyond creepy. What the hell Dean?!

In the midst of his sloppy mental breakdown, another little blue envelope popped up on the screen. Dean was almost too terrified to click it, but figured it was best to deal with it now than when he was sober and hungover in the morning. 

“Really? Thought I was the only one.”

Oh my god. Oh my GOD. Dean’s heart leapt into his throat. There was no way this was happening. His double vision was just fucking with him. He looked down to scrutinize the message once again, and sure enough, Cas had actually typed out and sent that message. Holy shit.

Within a matter of seconds, Dean hopped back onto his twin sized bed and adjusted the screen of his laptop. He was too excited at this point to care about how embarrassing it was, and clicked the search bar. “dark hair tutor gay”

A surprising number of results showed up when the page finished loading. Seventeen pages worth of videos fitting into the precise category of his repressed fantasy. After scrolling through three pages in search of the perfect match, he clicked on one. The thumbnail showed the back of some dude’s head, kneeling on the ground in front of a guy sitting atop a desk, papers and books pushed aside to make room. His hair looked almost exactly like Castiel’s and that was enough. Dean clicked. About a minute into the video, Dean was already about to finish. He bit his bottom lip and stifled a sinful moan, he knew he only had a few strokes left til he spilled all over himself and his sheets. Just then, the camera switched angles, ready for the cum shot. Dean froze, hand halting at the tip of his throbbing cock. An overwhelming sense of horror and ecstasy exploded within him as he shot hot cum all up his chest, drenching his shirt and and surprising him with the sticky mess reaching his chin. His own semen dripping off of his face, he choked on his saliva in shock. The dude looked exactly like Castiel. Like, exactly. He watched the rest of the video intently, the mess drying on his shirt and chin. As soon as the guy on the desk shot all over the Cas lookalike’s face, cum dripping off his thick-rimmed glasses, he heard the primal growl. That was Cas. There was no way that wasn’t Cas.

Dean hastily threw his phone across the room into a pile of clothes. One thing he knew about himself was that he was terrible at resisting drunk texts. He wouldn’t know what to say. He didn’t know what to think. What the hell did he just see?! 

After getting up to find a dirty shirt to wipe the mess from himself with, Dean stripped of his unreconcilable t-shirt, and laid down to sleep. Sleep didn’t come for hours, as he lay staring up the ceiling unable to stop his train of thought. Not only would monday be extremely awkward after his regretful text volley with Cas, but now he had to deal with seeing the guy after viewing him in a fucking porno. In a setting just like the video, nonetheless. Oh fuck.


	2. Pretty Boy Angel

**Summary for the Chapter:**

> Dean has to face Castiel after their run-in Friday night.
> 
> Also, it turns out he has a whole porn channel account.

**Notes for the Chapter:**

> Pretty much pure smut at the end.  
> Feedback is good, should I continue with this?

_Three minutes and twelve seconds_. As his final class of the day was drawing to a close, Dean had his eyes locked on the clock. The professor stood behind a podium at the front of the room, droning on and on about whatever the hell they were learning about in trigonometry that day. In one ear, out the other. All he could think about was the tutoring session he was about to attend. He had considered backing out of it, pretending to be sick, anything. However, if there was one thing Dean was not, it was a little bitch. He had to show up, no matter how uncomfortable it made him. If he cancelled, Castiel would know that Dean was ---- and he just couldn’t handle that reputation.

_Two minutes and four seconds_. Dean was sick to his stomach, his entire body tense with anticipation. This was hell. He tried his best to dress like he didn’t care- a ratty old Led Zeppelin tee shirt and some jeans still stained with motor oil. After all, he didn’t care, right? 

_Forty-five seconds_. Shit, he did care. He really cared. Anxiously bouncing his leg, Dean started taking some deep slow breaths to calm himself. As soon as the lecture came to a close, he shoved his blank notebook into his backpack alongside his textbook, and just about sprinted out of the room.

Dean had just about ten minutes before he had to meet up with Castiel in the library. Sneaking alongside the building, he reached into his pocket for his pack of cigarettes. Shit, he left them in the dorm. 

“Okay, Dean.” He muttered to himself, wringing his hands anxiously. “Keep it together, man. You got this.”

After his little pep talk, Dean sulked over to the front steps, weighed down by his backpack. Inside the almost silent building, Dean could hear his heart beating in his ears. He slowed down, hoping a leisurely pace would help to calm him. Nope. When he finally reached the doors to the designated study area, Dean took a deep calming breath. 

At the far end of the room sat Castiel tapping his fingers on his desk. He was a relatively calm person by nature, but the thought of Dean brushing their communication off as a drunken mistake was eating away at his brain. As Dean approached his study station with his eyes glued to the floor, Castiel’s heart sunk. He was ashamed. Surely he was coming to apologize or say the text was meant for someone else or maybe Castiel had just misinterpreted it and Dean didn’t eve--

“Hey Cas.” Dean’s striking green eyes smiled at him. 

Castiel smiled shyly up at Dean, praying to god he wasn’t blushing as much as his face felt like it was. “Hello Dean.”

And that was that. They got down to business, poring over the papers and books spread out between them. Nothing strange at all. No awkward fumbling with words, no mention of their interaction the other night. Castiel sighed with relief.

Dean, on the other hand, couldn’t for the life of him stay focused on the task at hand. Every time Cas pushed his glasses up on his nose, or ran a frustrated hand through his hair, Dean could only think of the video. As he watched Cas’ lips form words, all he could think about was how pretty they would look stretched around his cock. He let his mind wander, wondering if the table they were seated at was the right height for Castiel to reach him if he were on his knees. 

“Did you catch that?” Castiel’s steel blue eyes peered innocently up at Dean over his glasses. Dean immediately pictured those same glasses dripping with his cum. All he could think of was that damn video.

Glancing down at the graph Castiel had just drawn, all Dean could offer was a nod. Honestly, he hadn’t heard one word coming out of his mouth this whole time. 

Castiel put his pen down, and placed his hands face down on the table. “Dean?”

Suddenly, Dean felt very guilty. Not exclusively because of his filthy train of thought, but because poor Cas was spending an hour of his day trying to help him, and it had all fallen on deaf ears. Scratching at the back of his neck, Dean tentatively locked eyes with him. “What was that? Sorry.”

“Are you okay?” The low rumble of Cas’ voice went straight to Dean’s dick. Castiel furrowed his brow with concern. “We can pick this up again later, if you’d like to take a break.”

“I guess I just can’t focus right now. I’m sorry, man.” Dean mumbled. Hey, at least he was honest.

Still looking worried, Castiel gently closed the textbook, and stuffed his pens and notebook back into his messenger bag. 

The guilt continued to eat away at Dean, who was fighting hard to keep the obscene images from the forefront of his mind. On one hand, Dean wanted to grab Cas, turn him around, and bend him over the desk right now. On the other, he saw a nice guy who actually seemed to care about him. It was all so strange to Dean. 

All packed up, Castiel turned back to Dean and cleared his throat. “So, uh. Got any neat plans tonight?”

Dean fought the urge to laugh at Castiel’s usage of the word ‘neat’. What a fucking dweeb. “Nah, I’m pretty boring.”

“Would you,” Castiel cleared his throat, “Want to take this lesson elsewhere?” He averted his eyes, anxious about the impending response. 

“I-” Dean croaked out. He couldn’t believe Castiel had just asked him if he wanted to ‘take the lesson elsewhere’. “Yes, it might be easier to focus without all these people around.”

Twenty minutes later, they stopped by Dean’s dorm room. Castiel immediately settled himself in Dean’s desk chair and began to unpack his nerdy belongings for their study session. 

“Oh, sure. Make yourself at home, Cas.” Chuckled Dean teasingly, resisting the urge to shove all of the books and papers to the side and fuck Cas’ pretty little mouth. As he went to toss his backpack down on the bed, he saw his laptop wide open sitting atop his pillow. Oh shit. Dean dove on to the bed, sliding in and slamming the screen shut in one swift movement.

Castiel turned to Dean with a sly grin on his face. “Whatcha hiding there, Dean?”

“Nothing.” _Not a video of you blowing some dude_.

They sat together for about half an hour, actually studying. It shouldn’t have been a sexually frustrating activity, they were studying for christ’s sake. However, the whole time, Dean was putting an immense amount of effort into not jumping Cas’ bones. 

In the middle of explaining a particularly hard theory, Cas stood up abruptly. 

“Oh shit!,” his eyes opened wide with panic as he rummaged around for his phone. “Dean, what time is it?”

“Uh, just about 6:30.”

Castiel was already rummaging around, haphazardly shoving his belongings back into his messenger bag. “I’m really sorry Dean,” He was already halfway across the room, “I- I forgot I have work tonight. I got.. called in for a shift.” At that, Castiel pushed open the door and was gone in a flash.

Dean sat alone in the room, stunned for a moment. As he came back down to earth, his eyes widened with realization. Work. Like, the kind of work Dean had found on the internet? Or maybe he had some kind of normal nerdy job like a barista or something? There were so many questions still to be answered regarding that mysterious little nerd.

Shrugging off these thoughts, Dean kicked his shoes across the room and stripped off his jacket. Might as well watch that video for the fifth time. Just as Dean settled in, fly unzipped, he realized. Surely if Castiel had starred in a porno, there must be more. He must have a porn name or something. Dean spent the next few minutes clicking and following a trail of links til he finally landed on the page he needed. Not only was Castiel in a porno, but his member profile had links to several other videos. Preemptively, Dean shut the blinds of the window behind him, and pulled out his half hard cock.

Through further investigation, Dean discovered that Castiel’s username was ‘prettyboyangel’. What a fucking weirdo. Whatever, there were much more important tasks at hand (no pun intended). He scrolled to the bottom of the page, absentmindedly stroking himself and perusing the thumbnails. The last one on the page had a blinking red dot in the corner, and no image, just a black box. Hm.. After a few seconds, a green “LIVE” began to flash in the center. Dean took a deep breath, adjusted his position, and clicked.

So far, it was just a screen full of empty bed. Gray sheets were spread across the top of the mattress, a pile of pillows propped up in the corner. Oh my god. 

A fully-dressed Castiel, in the same exact clothes he had been wearing just fifteen minutes ago, climbed into the frame from the far side of the bed. He leaned over to adjust the camera on his laptop with a wink, and Dean stopped moving, totally transfixed. Castiel put his hands behind his head, leaning back against the pillows. 

“What do you guys have in store for me tonight?” He growled seductively. Castiel readjusted, crawling towards the camera and propping himself up on his elbows. He looked down out of view, and Dean heard a clicking sound. Just then, the live stream stopped, a white popup appearing in the center of the screen. On it was a green dollar sign, and a box to type in credit card information. Without a second thought, Dean lunged from his bed to grab the wallet out of his jacket pocket. He fumbled with the keys, typing as fast as he could. By the time he caught up with the video, Castiel was already stripping off his button-up shirt. This left Cas in white v-neck, through which his perky nipples were visible. Dean couldn’t peel his eyes from the screen. 

Castiel leaned towards the camera once more, clicking another key. A small chat box popped up in the corner of the screen. Still foreign with the concept of whatever was happening, Dean continued to watch in a daze. He heard a message alert sound, and watched as Cas squinted his beautiful blue eyes through his glasses to read something on the screen.

“Oh?” Castiel spoke in a low seductive tone. “You want to see me stroke it, baby?” He bit his lip and leaned back against the wall spreading his legs and running a hand down between his thighs. Within a matter of seconds, the bulge in Cas’ pants started to grow, and he continued to rub until he was completely hard. He snaked a hand down to his waistband and slowly undid his fly. Back against the wall, Castiel raised his hips to pull his pants down to just above his knee. He continued stroking himself through his black boxer briefs, breathing becoming audibly heavy.

Dean could not handle it. Castiel was such a little tease, and it was torture to watch him move so slowly. He waited another minute or so, til another message alert sounded. Pulling his glasses further down the bridge of his nose, Castiel peered across the bed at the message. 

He smirked into the camera devilishly. “Oh, so that’s what you meant.” Castiel slowly inched his boxer briefs down his slender hips, and Dean noted his sharp hip bones. God, he was so sexy. 

And there it was. Cas’ big beautiful cock sprang free, tapping against his stomach. God, he was huge. Dean thought he was going to die. Heart palpitating in his chest, he flicked his thumb over the slit at the tip of his cock to slick himself with precum, and began with gentle slow strokes. It was impossible at this point to stifle the groan that escaped his mouth as he ran his hand up and down his length, matching pace with Castiel.

Dean leaned to his side, propped up on an elbow, and continued to observe. Every little whimper that escaped Cas brought him that much closer to finishing. He doubted he could last much longer.

“Oh, come on,” Castiel moaned, still tugging at his cock. “Is that all you got?” 

After a moment of contemplation, Dean reached forward and pulled the laptop closer to his face. The things he wanted to watch Castiel do.. God, it felt so wrong watching this, never mind participating, but he paid for it so he might as well. Dean tapped at the keys with his free hand. 

_Finger yourself for me_.

Not a second later, another message sound. Dean wondered for a second if the quick reaction time was due to the fact that Castiel was probably in the same building as him. The thought turned Dean on even more.

Castiel stared into the camera, a sinister glint in his eyes. “Ohh.” He purred. 

Dean watched as he kicked off his jeans and positioned a supportive pillow beneath his lower back. Still staring into the camera-- which felt like direct eye contact and made Dean a little uncomfortable-- Castiel slowly inserted a finger into his mouth and pulled it out with a wet popping sound. Fuck. He trailed his other hand lazily across his chest and stomach, stopping momentarily to flick at his nipple. Cas’ lubed finger gently circled his hole as more filthy noises emanated from him.

Whimpering, Castiel began to press in. Dean whispered fuck as he watched on, hypnotized. After a few tries, Castiel had finally loosened up enough to slide his finger all the way in and out, slowly. He threw his head back, crooking his finger to hit his prostate. Castiel let out a primal growl, just like the one Dean had seen in the first video, and inserted finger number two. Dean watched intently as Cas stretched himself open, stroking himself faster in time with Castiel.

“Aah-” Castiel’s hips started bucking involuntarily. “I- unhh- please just-”

Watching Castiel clenching around his own fingers, Dean hurriedly leaned forward to type another message. 

_Cum for me Cas_.

Realizing the implications of accidentally calling him ‘Cas’, Dean freaked out. Nobody else watching this livestream knew his real name, let alone a nickname. His body went rigid, all color draining from his face. Oh shit, oh shit, oh shit. The message sound dinged again, and the split second between it being received and read felt like an eternity. 

Castiel squinted through his glasses towards the screen, and his mouth dropped open with shock. He stopped pumping his fingers for a moment and froze like a deer in the headlights.

“FUCK!” Dean didn’t know what to do. All the damage was done, this was it, his life was over. A thousand different anticipated outcomes flashed in his brain. Castiel was going to come over and yell at him. Castiel would be so embarrassed that he’d refuse to be Dean’s tutor anymore. He’d lose his friend. Oh god..

Instead, Castiel closed his eyes and reclined, spreading his legs even farther apart. Biting at his bottom lip, he continued to work himself to completion, grinding down on his fingers. Dean was shocked. Absolutely shocked. His shock was quickly replaced with overwhelming arousal as Castiel gripped at his own cock, slicking himself with precum and pumping fast and hard. His thighs began to quake as he frustratedly bit at his bottom lip, letting out a sharp hiss. Castiel was close. Very close. Suddenly, the look on his face transferred from frustration to pure ecstasy. His mouth moved wordlessly, gasping for air and whining desperately for release. Cas rode out his orgasm, jerking up into his hand as ropes of hot cum spurted out, painting the front of his tee shirt. Dean wasn’t positive, but he swore he could hear his name intermingled with the deep steady breaths that followed. Watching Castiel’s chest rise and fall, paralyzed in the afterglow of his release, Dean’s focus shifted to his own erection, and the all familiar sensation settled in his core.

Eyes still on the screen, enjoying the look of pure bliss on Castiel’s face, Dean worked his hand over his cock faster and faster til he finally spilled, the sticky mess running down his chest and knuckles, white lights dancing across his vision. He was forced to tear his gaze from the screen as his eyes willed themselves shut, whispering Cas’ name with every shuddering wave of ecstasy. By the time Dean’s temporary paralyzation subsided, he peered back over at the screen. Cas was gone. 

“Well, that was awkward.” he spoke aloud to himself in his empty dorm room. “Fuck.”

As Dean made his way over to the pile of dirty clothes in the corner, finding a tee shirt to clean up his mess, he heard his phone chime in the pocket of his jacket. 

_1 New Message from Cas_

Dean clamped his eyes shut, preparing himself for whatever proclamation of anger he was about to receive. He sucked it up and tapped on the flashing blue envelope.

_Don’t judge me, I need the money_

Oh no, he embarrassed Cas big time. Poor kid was just trying to make some money on the side secretly, and Dean blew his cover. Strong pangs of guilt struck Dean, he knew he shouldn’t have done this. Why did he have to be so stupid as to refer to Cas by his first name? Shit.

Another message popped up

_but let’s team up next time. I want you to make a mess of me._


	3. Two Way Street

**Summary for the Chapter:**

> Dean owes Cas.

**Notes for the Chapter:**

> veryveryfilthy

“What the fuck dude!”

The impact of the pillow across his face smacked Dean right out of his sleep. It was a shame, he was right in the middle of one of his grade A lucid dirty dreams. 

He squinted his eyes, blinded by the light of the lamp on his bedside table. “H-huh?” 

Dean’s roommate, Gabriel, was backed up against the wall on the other side of the room, brown eyes open wide and eyebrows basically hitting the ceiling. “Clean that shit up, man! Nobody wants to see that!”

Groggily tilting his chin down to figure out what the fuck Gabriel was talking about, Dean took in the dry white mess covering his chest and stomach. His laptop was still open, but thank god the screensaver kicked on. Dean groaned and threw back his head, shamefully throwing a pillow over his face. 

“Shit, I’m so sorry man.” Dean apologized, voice muffled by the pillow. His hands reached down and swiftly yanked the sheet up over his body. “What time is it?”

He was answered by the slamming of a door as poor Gabriel stormed out of the room, traumatized. Dean fumbled with his phone, clicking the unlock button to reveal that it was 11:24. Also displayed on his screen was the all-too-familiar flashing envelope, informing him that he had 7 unread messages from Castiel.

_please don’t tell anyone else you found me on there_

_maybe you should return the favor ;) you can make a private account ya know_

_actually i think i need that. god damn i want to watch you touch yourself right now_

_i want to hear the noises you make_

_god, that was a creepy thing to say. i understand if you want to find a new tutor._

_are you there, Dean? i’m sorrry_

_god i really fucked up this time_

 

The last message sent by Castiel was time stamped 9:53 pm. Shit. He wanted to text Cas back and let him know that he was in fact _not_ being too creepy. Dean didn’t know just how to respond to the messages, so he got up to clean himself off and mulled over some responses in his head. Dean threw on a clean t-shirt and a new pair of boxer briefs and sauntered back over to his bed, smirking to himself.

When he tapped at the Enter button on his keyboard, the screen illuminated. The video box where Cas had been teasing him a few hours earlier was black with “live stream interrupted” displayed. Dean didn’t have to think twice before all the blood in his head rushed south and prompted him to do what he was about to do next. He clicked on his username, opening the account preferences. It took him a few minutes to figure it out, but when he found the “create channel” link, he bit his bottom lip and filled out the necessary information. Nerves tightening into a knot in his stomach, Dean hovered over the “start a live stream” button and clicked. He triple checked that his channel was password protected before moving his thumb from over the camera hole embedded in the laptop’s screen. 

Dean got up to make his bed, placing the open laptop on the chair beside it so as not to fling it off the mattress in haste. It all looked pretty put-together for the most part aside from a conspicuous stain, but with a meticulously placed pillow, everything appeared to be fine. Leaning over to snatch his laptop, Dean froze for a second and smiled. What better place for a ‘tripod’ than a chair? Before hopping up on the bed, Dean swiped his thumb over the camera hole to get a clearer shot.

He made himself comfortable, pillows stacked for back support and legs sprawled out across his sheets. Taking a deep breath to steady himself, Dean picked up his phone and opened a new message to send to Cas. 

_sorry man. i passed out_

 _but maybe this will make up for it. password is_ yourewelcome

Squinting back and forth between his laptop and phone, Dean copied the link for the live stream into the text box and hit send.

A few minutes later, a new message from Castiel popped up.

_oh my god. give me five minutes._

The urgency conveyed by Cas’ message brought a smug look to Dean’s face. He couldn’t wait to see Castiel’s reaction to the show he was about to get. Worrying about their relationship after this night seemed no longer an issue. Nothing could get in the way of two guys and their needy cocks.

Taking advantage of his alloted prep time, Dean started to rub at his half-hard cock through the cotton of his boxer briefs. He worked himself slowly, closing his eyes and reveling in the friction. After a moment, he peered down at the bulging outline, suddenly self conscious. What if Castiel didn’t like it? What if he thought it looked funny? In any other situation, Dean would be too focused on the task at hand to even give it a second thought, but what-

Dean scooped up his phone on the first ring. It was Cas. Shit.

“I’m ready for you, Dean.” Cas’ low husky voice whispered into his ear through the receiver. The sound alone was enough to make Dean’s cock twitch.

“Heya, Cas.” His voice came out awkwardly, in an attempt to sound seductive.

Castiel groaned on the other end of the call. “Stay on the phone while I watch you.” It wasn’t a question, it was a command.

Before Dean had a chance to respond, there was a small ding and a message popped up on the screen. _1 Live Viewer_

Not used to being watched like this before, Dean shot an awkward half-smile at the camera, and sat there like a deer in the headlights.

Cas chuckled in his ear. “Do you need me to direct you?”

Dean bit his lip and nodded innocently.

“Don’t play coy with me Dean.” Castiel continued, not covering up the unmistakable sound of a zipper coming undone. He shuddered as he pulled out his half-hard cock.

Closing his eyes and swallowing, Dean reclined, giving Cas a shot through his legs at the throbbing erection straining beneath the thin cotton of his underwear. It twitched at the sound of another small groan escaping Castiel.

It took a few seconds to get comfortable, but Dean started to relax as he worked his hand over the bulging outline. He gripped harder at every small whimper emitting from Castiel. 

“ _Unhh_ ” Cas breathed, obviously aroused. “Let me see that beautiful cock of yours, Dean.”

All inhibitions were thrown out the window as Dean pushed the waistband down below his balls, cock springing free heavy and leaking against his stomach. They both hissed as Dean trailed a hand down his chest, pinching at one of his nipples, hips bucking forward at the surge of arousal. Placing the phone next to his head on the pillow, Dean gripped at the sheets with one hand, and wrapped his other around his cock.

“ _Fuck._ ” 

Castiel’s reaction sent another hot wave of arousal surging through Dean. He swiped a thumb over the bead of precum collected at the slit, and slicked his cock, running his fist up and down slowly to lubricate. 

“God dammit Cas,” Dean spoke huskily next to the reciever. “Feels so good.”

“ _Dean_.” Castiel’s voice sounded wrecked, he was definitely jerking off to this. “I want to see how you touch yourself when no one’s around.”

Without hesitation, Dean raised a palm to his mouth and spit in it. Cas was losing his mind over the phone. Gripping harder at his cock this time, Dean quickened his strokes and curled his toes into the mattress. Each pass of his fingers over the sensitive tip of his cock drew a sinful moan from Dean, starting off low and modest til he was shouting out curses. The knowledge that Castiel was both watching him and commanding him had Dean’s cock downright throbbing in need of release. 

“Yeah. Yes. Just like that.” Castiel grunted through the phone, fist audibly slapping against his skin as he desperately jerked his own cock.

Dean’s breaths got deeper and faster, knowing that he wasn’t going to make it much longer. “F-fuck. I’m really really-” he let out a sinful little whine.

“Stop.”

Furrowing his eyebrows in confusion, Dean kept going. “What?”

“Stop.” Castiel spoke in a more commanding tone this time.

Begrudgingly, Dean tore his hand away, cock throbbing against his stomach in need of release. He let out a high-pitched whine which nearly brought Cas over the edge.

“Good boy, Dean.” 

The command coupled with words of praise had more of an effect on Dean than he would have liked to admit. Thoughts of Castiel overpowering him had his eyes rolling back into his head with pleasure and his cock pulsing harder. It bobbed against his stomach, threatening to give way at any second.

“Now.”

Dean’s ears perked up, eager to take any direction from Castiel he was given.

“Put those tight little boxer briefs back on.” Cas mischievously directed him.

“What the fuck, man?” Dean groaned. Why did Castiel have to be so cruel?

Cas breathed heavy through the phone. “Do as I tell you.”

With a voice like that, how could Dean not? He snapped the waistband up over his erection, whimpering at the feeling of the tight material over the sensitive bulge. 

“Cas,” Dean spoke desperately into the phone. “I am seriously so fucking close.”

A dark chuckle coming from under his breath, Castiel continued. “Oh, you’re not the only one. I’ve got my cock out, all slicked up and waiting to cum for you, Dean. I’d love nothing more than to give you that satisfaction.”

Dean’s cock pulsed harder, twitching up against the thin cotton constraints of his underwear. He shuddered at the feeling.

“Can you do just one more thing for me? Please?” Cas purred in a pseudo-innocent tone. 

“Yes. What?” Dean frustratedly gritted out through his teeth.

“Cum for me, Dean.”

Castiel’s voice halted him as he reached down to free his trapped erection.

“Did I tell you to take it out?” Castiel’s voice sounded downright evil. He had to be evil to suggest such a thing.

Letting out a huff of breath, Dean relaxed back into the pillows and placed a hand over the bulge in his underwear. He moaned at the sudden return of pressure, tugging up and down at the hard line pressed against his stomach through the fabric. Despite the impending mess, the friction felt better than he could have ever imagined, and the familiar hot knot of pressure settled just above his groin.

Apparently, this greatly pleased Castiel, who was groaning in time with his hand as he fucked up into his fist on the other line. “ _Jus-_ Just like that Dean.”

Dean rubbed circles over his cock, massaging up and down through the tight fabric, precum spurting out to form a wet spot that felt amazing against the super sensitive tip. 

“God dammit Cas,” Dean’s breaths quickened, whimpering between words. “I’m right there. I’m right there.”

In an uncharacteristically high pitched voice, which signified his impending orgasm, Cas gave one more command. “Come closer. P-Please Dean,I-- _uunh-_ let me watch. Please.”

Abruptly propping himself up on his knees, Dean inched closer to the screen, leaning back on one hand and working himself to completion with the other. Grasping through the fabric at his cock, Dean seized up, grunting out Cas’ name as he sputtered, cum spilling out and seeping through the fabric. He gave two final jerks, sweat dripping down his neck and his load providing good lubrication to ride out his orgasm.

Cas’ voice hitched, orgasm pounding through his veins as he milked his cock and covered his fist and dress shirt in the hot sticky mess. All the while, an audible shudder running through his body as he all but screamed Dean’s name, repeating it several times as it was slowly reduced to a whisper.

Finishing off his performance, Dean gently ran a hand down his overly sensitive length, one last cry of pleasure escaping his throat as he reached down and clicked the “end live stream” button.

It took a few moments of heavy breaths and recollection before either of them spoke.

“See you tomorrow at 4.”


	4. Elephant in the Room

**Summary for the Chapter:**

> The day after

**Notes for the Chapter:**

> Not sure if I want to continue on from here, but I think it's a definitive turning point in the story.
> 
> Does anyone want more? I could go either way.  
> The future holds smut if I end up doing more.
> 
> Either way- thanks for reading :)

After coming down from the high of last night’s filthy interaction with Castiel, Dean’s anxiety had weaseled its way back in. They were about to meet face-to-face for the first time since ‘the incident’. Last time they’d been together had been before Cas even knew he was being watched by Dean, and now they’d watched each other jerk off. Not only that, but Dean followed Castiel’s instruction, leading to the shameful spectacle of getting off inside his underwear. Had Cas intended to humiliate him? It was starting to feel like it. 

Dean sat at their regular study table at the back of the library, anxiously tapping his chewed up pen against the dinged-up wooden table top. He glanced up at the clock, almost afraid to check the time. 4:04. Part of him knew it was silly to worry, and that he himself had been later than this to meet up for their tutoring session, but his lack of self-confidence was starting to get the best of him. Cas wasn’t coming. 

With a sigh of resignation, Dean piled his notebook on top of his trigonometry text book, and slid them into his messenger bag together. While he was bent over, arranging his belongings in the bag, he heard a _tsk_ from a few feet away.

“Hold up.” Castiel raised a dominative eyebrow. When Dean obeyed, pulling his books back out and laying them on the table, Castiel smirked. “Good boy. You’re not getting off that easy.”

Jesus Christ. Now Cas was just trying to punish him. 

Dean scratched the back of his neck, trying to ignore the burning blush spreading across his cheeks. “Sorry, I didn’t think you were coming.”

Without a response, Castiel settled himself in across the table and pulled out a notebook and a pen. They sat in silence for what felt like ages, both tapping their pens and going out of the way to avoid eye contact. 

“Okay, Dean.” said the all familiar rumble of Cas’ voice. “Which chapter are you on now?”

Oh god, that voice went straight to his cock. “Uh- um, thirteen.” 

Distracted by the homework, things became a little easier. Not that the situation wasn’t still horrifically and paralyzingly awkward, but at least Dean felt comfortable talking. Throughout the session, their eyes were kept to themselves, focusing only on the task at hand. They got through a big chunk of the chapter, working through different types of questions until Dean felt like he actually had a grip on what he was supposed to be learning in class. 

Though it was a relief to ignore the reality of their situation for a while, the elephant in the room started to eat away at Dean. They couldn’t just ignore this forever. Dean began to sweat profusely, hands shaking, and his throat felt like it was closing up. He knew he would have to face Cas again, but he wasn’t prepared for this. It just wasn’t fair. Castiel sat across the table, cool as a cucumber. Of course Castiel was more relaxed. He spent his free time jerking it online for money. Not only that, but Cas hadn’t just cum in his fucking boxer briefs to give his tutor a show. He was downright humiliated. Castiel was just punishing him, trying to make up for the embarrassment he felt when Dean found his live stream. Dean’s brain started whirring faster and faster, too many thoughts tugging at his brain in different directions.

During a particularly frustrating equation, Dean threw his pen down on the table and abruptly stood up. Castiel looked on, borderline terrified, as Dean paced back and forth tugging frustratedly at his hair.

“What the fuck, man?!” In the midst of a panic attack, Dean had no control over the volume of his voice, drawing glares from the students scattered around the library.

Not knowing what the hell to do, Castiel shushed him and rose from his seat. Dean clamped his eyes shut, knuckles white clenched around tufts of his hair. 

“What’s going on, Dean?” Cas spoke quietly next to his ear, hoping to avoid a full-fledged scene. “Are you okay?”

Realizing just how crazy he made himself out to be, Dean started shaking with frustration. He blew it. He absolutely blew it. There was no way to backpedal now, he just lost any chance he had at playing it cool. He took a few deep breaths, trying to muster up the clarity of mind to save any shred of dignity he could possibly have left. It was no use. He hadn’t had a panic attack this bad in years, and even back then had never quite figured out how to talk himself out of it. 

“Dean?” resting a placating hand on Dean’s shoulder, Castiel looked on, worried. “Wanna go get some fresh air?”

Instead of a verbal response, Dean opened his panic-stricken eyes and nodded furiously. Castiel followed Dean’s lead as he tore through the library, making a beeline to the building’s front doors. 

“Dean..?” 

Following him down the stairs and around the corner of the building, Cas watched on in confusion and fear. Dean patted down his jacket’s pockets, pulling out a lighter, and frantically fumbling in search for his pack of cigarettes. When he didn’t find them, he threw the lighter down on the asphalt so hard that it threw sparks.

Castiel cleared his throat awkwardly. “Need a smoke?” He quickly procured his own pack of cigarettes from his hoodie and handed them over to Dean.

Cigarette trembling between his lips, Dean bent over to pick up his lighter and flicked it several times before the tip of his cigarette glowed red. Immediately, he felt calmer. Blowing the first drag out through his chapped lips, Dean let out a pitiful self-mocking laugh. “Well, that was smooth.”

“Ha.” Castiel sucked in through his cigarette, ensuring it to be lit. “What’s going on, man? Is this because of last night?” He looked down at his shoes. Dean wasn’t the only one feeling completely mortified by the experience. 

Dean carded a hand through his impossibly disheveled hair. “Yeah, I just-” He looked up to tentatively meet Cas’ gaze. The look of worry with which Castiel was regarding him set him at ease. “I’m sorry for being such a creep. I deserve to feel like this.”

Suddenly Castiel was standing in his personal space, cigarette pinched between his thumb and index finger. As he reached up to rest a soothing hand on Dean’s shoulder, Dean flinched. 

“I’m not sure exactly what you mean by that, Dean.” Cas flicked the butt of the cigarette, ashes dancing from the tip. “However, I can tell you’re not feeling good. Which is never something that I would wish upon you. I am sorry for overstepping a very important boundary.”

Taking a long drag from his cigarette and blowing it out, Dean straightened up. “I was the one who found you. How creepy is that shit?” He asked rhetorically. “Very creepy. God, this is all my fault.”

Cas shook his head, drawing in another hit of nicotine. “I didn’t think it was creepy of you.”

Dean shot him a look.

“Okay, maybe a little creepy.” Shifting uncomfortably on his feet, Cas continued. “But god dammit Dean. That was the hottest thing I’ve ever seen.”

Apparently anticipating a completely different outcome, Dean sputtered, smoke catching in his throat. “You really think so? My little freak out just now didn’t change your mind or anything?”

“You really have nothing to be ashamed of.” Castiel leaned in close, lips just centimeters away from Dean’s ear, purring. “It’s all I can think about. Want to know something embarrassing?”

Heat rising to his cheeks, Dean shook his head. 

Castiel took a step back, holding Dean’s face still in his hands and locking his eyes in a mischievous gaze. “I..” 

Dean’s eyes widened and his mouth went dry. 

“You have no idea what you do to me, Dean.” Castiel crooned, cradling Dean’s face in one hand, the other reaching up to smooth over his hair. “After seeing you like that last night, I just couldn’t handle it any more. I spent all day trying to get images of you out of my head. Couldn’t pay attention in any of my classes. All I could think about-” Cas trailed his hand from the side of Dean’s cheek down over his mouth, gently pulling down Dean’s lower lip with his thumb. 

Frozen in shock, Dean watched on, chest rising and falling with shallow breaths.

“I had a dream about you last night. The kind of dream you wake up from covered in your own cum.”

“Holy shit, Cas.” Dean whispered. He couldn’t believe how quickly he went from an anxiety attack to a raging boner.

“I know, right? It’s like I’m 13 or something.” Castiel looked ashamed. “I just- Sorry if that’s TMI or something. Just thought it might help to make you feel less embarrassed about the underwear thing.”

Dean chuckled uncomfortably. He was so aroused by Cas’ filthy confession that he couldn’t focus on being embarrassed long enough to let it bother him anymore. It was becoming impossible to focus on anything but his now-throbbing erection.

“Cas,” Dean decided he might as well go out on a limb. 

Eyes stuck on Dean’s plump lips, Castiel nodded.

“Let’s get our stuff and head out of here.”

“Yeah?” Cas looked up to meet Dean’s eyes, pupils blown and hungry.

Dean subconsciously groaned, taking in the sight. “I don’t want to do this through a computer screen anymore.”

Biting his bottom lip, Castiel nodded furiously. “Me neither.”

Back in the library, they each scooped up their belongings and shoved them into their respective backpacks. Just as Dean turned to push his seat in, Castiel snuck up behind him and whispered in his ear,

“I can’t wait to get that beautiful cock down my throat.”


	5. This is it

**Summary for the Chapter:**

> Not gonna lie, this is just straight up porn.

Clamoring around his dorm room like a baby horse, Dean hurried to get everything in order. After their tutoring session, he and Castiel agreed to take a quick break and meet up again at Dean’s dorm. Dean pulled the sheets tight and tucked them under his mattress, fluffing his pillows and throwing them into a haphazard stack in the corner. 6:01. Castiel was set to arrive in 14 minutes. 

Dean nearly slipped and knocked himself out as he sprinted to the communal bathroom, scoping out an empty shower stall and dumping his shampoo and bodywash bottles down on the tile floor. Things were all still a blur, but he knew one thing. He was about to have his tutor’s hot wet lips wrapped around his cock. Dean shivered at the thought. As he stepped under the near-scalding stream of water, he quickly lathered up his hair, then body, and tried not to give in to the bodily sensations of bathing. The flow of warm water that carried the soap suds down the curves of his abdomen was almost too much, he was absurdly aroused.

Within 3 minutes, he was ready to hop out of the shower. Not even bothering to properly dry himself off, he wrapped the warm fuzzy towel around his waist, grabbed his bottles, and padded his way back to the room. It was hard to resist the temptation to drop his towel immediately and wrap a warm hand around his already half-hard cock.

“C’mon,” Dean absentmindedly reprimanded his erection. “Chill out.”

He stuffed himself into a clean pair of gray jeans and a button-up flannel. Might as well look like he’s not a slob, even if he is. The clock by his bedside read 6:10. In an attempt to calm his nerves, Dean sat at his desk and rearranged the assorted papers and trinkets he kept there. As he was fidgeting with a matchbox car his brother Sammy had given him when he left to go to school, a timid knock came on the door.

Dean cleared his throat. “Come in!”

“Hello Dean.” Castiel’s voice sounded deeper than usual, surely he was trying to push all of Dean’s buttons. He slid through the doorway and latched it behind him. 

“Heya Cas.” It was hard to play it cool when the subject of all Dean’s jerk off fantasies was standing before him, in his own room, dressed like the huge nerd he was. 

Smugly, Cas adjusted his thick-framed glasses on the bridge of his nose. He watched Dean’s eyes hungrily rake over him, mindlessly picking pills from the front of his gray cashmere sweater vest. 

“Where can I--” Castiel scratched the back of his neck as he waited for permission to sit down on the edge of Dean’s bed.

“Uh,” Dean cleared his throat again, “Yeah, come on in, wherever you want. Sit-- if you want, anywhere.” He blushed at the complete lack of eloquence.

Sinking into the mattress, Castiel popped his shoes off and sat cross legged across from where Dean was stationed in his desk chair. 

They cleared their throats simultaneously, each waiting for a queue from the other to initiate something. It just made it more awkward. 

“Okay, Dean.” Castiel gazed over the rim of his glasses, eyebrows cocked. “You have three seconds to get over here before I jump you.”

Dean hopped up from the chair so fast he almost got whiplash, and landed on the bed with a thud. Castiel turned, face a mere few inches from Dean’s. As soon as Dean closed his eyes, Cas did the same, a hand grasping at the back of Dean’s head, pulling him deep into a kiss. Dean swiped a tentative tongue across Cas’ lips, initiating a series of long and drawn out kisses. The slow, tedious pace didn’t keep up for long. 

The mattress bounced beneath them as Castiel took control, straddling Dean and pushing him onto his back. Dean wriggled underneath his weight, watching Castiel as he licked his lips, staring ravenously down at Dean, where he was held captive by the unrelenting pressure Cas’ hands on his chest. 

“I want you to stay right where you are, Dean. You lay back and let me take care of you.”

Dean nodded enthusiastically and whimpered under his breath, hips involuntarily rutting up into the space between them. Something sinister shined in Cas’ eyes, but was quickly replaced with resignation as he propped himself up on his elbows hovering above Dean. Trailing soft kisses along Dean’s throat, he cautiously lowered his body so their erections were lined up. The slightest amount of friction was enough to have them both bucking against each other, a string of moans and whimpers hanging in the space between them.

 

Fingers woven in Dean’s damp hair, Castiel pushed his hips forward, grinding down hard against his cock. Dean whined, the needy sound almost pushing Castiel over the edge as he continued working up the friction between them. Reaching down with his hands to get a hold of Cas’ ass, Dean nipped at his lower lip, biting down and pulling away from Castiel, eliciting a deep guttural groan. They lay there for several minutes, pulling each other closer, seeking more and more friction, the silence of the room filling up with heavy breaths and pleading whimpers. 

“Mm- fuck,” Cas managed to separate from Dean for a second, propping himself up on his elbows once again. He snaked a hand between their bodies, resting it on the bulge trapped beneath Dean’s fly, applying pressure. His voice came out low and needy, craving the taste of Dean. “Please, Dean. Please. Please.”

“Yess,” Dean hissed his consent.  
Deftly maneuvering his fingers under the hem of Dean’s button-up shirt, Cas pushed it up his abdomen, revealing a delicious sliver of his stomach. He planted a trail of kisses down below his navel, stopping to focus on a certain point, sucking and biting til he left a mark. Underneath him, Dean was squirming, dick twitching against the fabric of his pants where it was trapped. Castiel reached down, quickly unbuttoning and unzipping Dean’s fly. He pulled his pants and boxer briefs down, cock springing free, heavy and thick. Moaning at the delicious sight, Cas wrapped a warm hand around the base, leaned forward, and licked a torturously slow stripe up the underside of Dean’s cock. This drew a filthy and pathetic pleading sound from Dean, whose whole body was shaking in anticipation. This was it, all he had been fantasizing about for the last few weeks. Every shower jerk off, every wet dream, every day when he woke up with morning wood, this was it. 

Without apprehension, Cas licked his lips, parting them slightly and wrapping them tight around the tip. He looked up over his glasses to meet Dean’s eyes as he took in his beautiful throbbing cock, sinking it into his mouth torturously slow. Dean writhed beneath him, eyes now clamped shut, all his energy put into not finishing too soon. Castiel quickened the pace, bobbing up and down on Dean’s cock, tongue working its way up and down the shaft as he moaned, savoring Dean’s distinct taste. Every moan vibrated through Dean, bringing him closer and closer to climax. Cas pulled off of Dean’s cock, the lack of suction making a popping noise. The sight was too much for Dean to take- his hot tutor, sweater vest, glasses and all- leering over him, mouth dripping with a mix of saliva and precum. He bit at his bottom lip, nodding desperately for the sensation of Castiel’s mouth, hot and wet, to return. Eyes locked on each other, Cas used the wet mess lingering on his lips as lube while he dove back down, lips forming a tight o shape as he stretched his mouth around Dean’s needy cock. 

Dean’s hands roughly gripped at the mess of black hair on the back of Castiel’s head, holding it in place as he fucked up into his mouth. Another muffled moan escaped Castiel’s mouth around Dean’s cock, breaths coming uneven as Dean pistoned in and out from between his lips. As he reached an uncontrollably frantic pace, Dean held Cas still and pulled out from between his lips, his thick wet tongue following him out, lapping at the tip.

“Cas, I’m gonna-” Dean’s warning was cut short while Castiel hungrily engulfed his cock, wrapping a hand around the base to match the movements of his bobbing head and swirling tongue. Cas could see it in Dean’s eyes, there wasn’t much time left. 

Hand now sliding up and down the length of Dean’s shaft, Castiel looked up at him, licking his lips. “Come for me baby. Please. Wanna taste you, fill me up Dean.”

Dean groaned, louder than intended, as Castiel lined up his parted lips, taking Dean in deeper, gagging as the blunt tip of his cock hit the back of his throat. Within a matter of seconds, Dean was pulling hard on Cas’ hair, holding on for dear life as his hips stuttered and he shot hot cum down Cas’ throat. Castiel lapped at Dean’s cock as he rode through his orgasm, moaning around him as Dean cried out, a stream of curses intermingled with Cas’ name. When Dean pulled out of Cas with a pop, the last of his semen spurted out across Cas’ lips. His tongue darted out, licking up every last drop.


	6. Rise and Shine

**Summary for the Chapter:**

> filth.  
> thank you so much for the kudos and comments I've been getting! Keeps me going :) You guys are great, enjoy!

What is that scratching noise?

Dean’s eyes blinked awake, confused and assessing his surroundings. He was in his dorm room, the light was on, and he was still wearing his clothes from earlier. His eyes drifted in the direction of the scratching noise, which had not just been a dream. There at his desk sat Castiel, brows furrowed, furiously scrawling in an open notebook. 

“Hello Dean.” Castiel greeted him casually, offering a polite smile. As if this whole situation was completely normal. 

Still hazy, Dean squinted his eyes in confusion. “What the hell is goin’ on, Cas?”

“Ha.” Castiel let his pen drop to the desk and turned to face Dean. “You’ve been out for a while now, I figured I would be a good tutor and help you with your trig homework.”

“Wait. Shit.” Dean sat up abruptly, incredulous for several reasons. “You- Oh my god, I just passed out and left you here? You stayed? Are you doing my work for me right now?”

Cas looked pleased with himself, crossing his arms over his sweatervested chest. “Yes, yes, and yes.”

Dean blushed, suddenly very interested in the pattern on the vinyl floor. “I’m sorry, man. But, uh, thank you. For the.. and the homework. You didn’t have to do that.”

“I don’t _have_ to do anything, Dean. I wanted to.” Castiel licked his lips, which sent Dean’s mind right back to the filthy place it was before he fell asleep. “Do you still want to hang out? I can totally head out though, it’s probably weird to wake up to me still here. I overstepped my boundaries, didn’t I? Shit.”

His insecurities were shushed by a rather aggressive kiss from Dean, who had his head set on thanking Castiel in his own special way. After the initial shock of being pounced on, Castiel eased into the kiss, moaning softly into Dean’s mouth as he slid his tongue in between Cas’ lips. It wasn’t long before Dean was on top of him, straddling Castiel’s lap and nibbling at his neck. 

“Dammit, Cas.” Dean murmured between kisses, “You were so good to me- Mouth felt so good around my cock- Wanna taste you.”

Castiel was too flustered to offer a response, sitting frozen in place as he watched Dean detach, lower himself to the floor, and settle on his knees between Cas’ legs. His swelling dick twitched in his pants, fighting to escape. “You don’t have to do this, Dean.”

“I don’t _have_ to do anything,” Dean winked, being a snarky asshole and stealing Castiel’s line from earlier. He leaned forward, nuzzling his face against Castiel’s erection, licking his lips and reveling in the noises he earned. 

He wasted no time, fingers working at Castiel’s fly, roughly yanking his pants and boxer briefs down to his ankles. Castiel’s cock bobbed in the air, red and already leaking with pre cum. Dean had only seen it on his computer screen, and here it was, mere inches from his face. Inhaling Cas’ distinct clean smell, Dean’s eyes lingered in awe. It was beautiful. 

Castiel muffled a moan as he bit at his bottom lip. Dean was taking in the sight of his cock with such reverence, it only turned him on more. He had fantasized about this moment for weeks, ever since he met Dean. So many nights spent alone in his bed or on his webcam, shamelessly finishing, spurting cum all over his stomach, Dean’s name on his lips.

Licking his lips and taking a deep breath to prepare himself, Dean closed his eyes and leaned in. First, he laid a kiss to the tip, starting off slow. Trailing wet kisses up and down the shaft tentatively, Dean kept his eyes on Cas’ face for any indication of how he was feeling. He didn’t want to admit to Cas that this was his first time, and hoped that his lack of finesse didn’t give him away. Judging by the way Castiel was already panting, and the way his fingernails dug into Dean’s shoulders, he was doing all right.

“Dean,” Castiel breathed out, bearing into him with an animalistic stare. “I’ve been thinking about this for so long.”

“Oh yeah?” Gazing up at him, Dean wrapped his long fingers around Castiel’s cock, grinning wickedly as the sensation earned a hiss from Cas. “What else do you think about?”

Castiel whimpered, hips thrusting forward, seeking the friction he needed. “Please, Dean. Please.”

Chuckling to himself, Dean quickened the pace. “I think about you too, Cas.” He offered an open palm to Cas. “Spit for me, baby.”

“Oh-- fuck!” Castiel obeyed his orders, straining to keep himself together as Dean brought him closer and closer to orgasm. He’d never taken orders from someone in person, just anonymously online, and then he was getting paid. This felt so personal, so real. “I think about a lot of things, Dean. You-- doing a lot of things.”

“Mmm,” Cas’ response seemed to turn Dean on even more as he licked a stripe up the underside of his shaft, dick twitching in response. He wanted- no, he needed- more attention from Dean’s teasing tongue. 

“I think about you sucking my cock. All the time.” 

Dean smirked up at Cas, keeping their eyes locked as he pressed his tongue against the sensitive tip of his cock and lapped at the pre cum leaking out of him. “Tell me what else, Castiel.”

The use of his full name made Castiel shudder, Dean’s low rumbling voice making the word sound filthy. He tried to keep a somewhat-clear head, struggling with the sensation of Dean’s mouth now circling around his tip, hot and wet. “Sometimes, when I- um, touch myself.” Cas scratched the back of his neck in a millisecond of awkwardness, which was immediately eclipsed by the ecstasy of Dean’s lips inching farther down his cock. “Unhh, fuck!- I think about you, all prepped and eager..”

Dean moaned again, the vibrations bringing Cas dangerously close to the brink. He detached himself, hunger in his eyes. “And then what, Cas?”

“And then-” Castiel was quaking, every muscle in his body seizing with the threat of imminent release. “You,” He held Dean’s face in his hands, tilting him up to meet his downright ravenous gaze. “Sinking down..”

He couldn’t wait to hear the end of Castiel’s sentence. Dean ripped his head free from Cas’ grip, desperately working him in and out of his mouth, swirling his tongue in all the same ways Cas had done for him- knowing how awesome it was feeling for Cas.

Castiel squealed, the sound making Dean all the more eager to rock his world and suck him dry. He began to pant uncontrollably, sucking in air and hissing it out, hips rocking erratically as Dean introduced a hand, coupling his movements with those of his mouth and tongue. “Oh, fuck. Oh fuck-ohfuck-”

All Dean could offer as a response was a muffled moan, matched with the sloppy sounds of his fists working up and down the pre cum and saliva slick he had built up. “Y- you- si-sinking down,” it took all of his effort to keep speaking, but he knew that Dean was loving every moment of it. “So tight, Dean. Sososo tight.”

Cas’ filthy words worked, Dean bobbed his head even faster, gripping at Castiel’s hip bones for leverage as he pounded down on him with his mouth. If his orgasm weren’t at the forefront of his mind, Castiel might have even stopped Dean to make sure he wasn’t hurting himself. But that did not matter.

“Dean- DEAN!” Castiel cried out as his body tensed, waves of pleasure rolling through him as he watched Dean swallow him down like a champ, reveling in every last drop of his sweet release. “Oh- my- god.” Cas threw his head back, gasping for breath as he slowly came down from his high.

When he could finally see straight, Castiel looked down at Dean, who was still knelt on the floor beneath him, head tilted with a very strange look on his face. Oh no..  
“What’s wrong Dean?” Oh shit, he had gone too far with the dirty talk. 

Dean scrunched up his face, “What a strange taste..”


	7. Making up for it

**Summary for the Chapter:**

> Castiel makes things up to Dean

**Notes for the Chapter:**

> I obviously have some kind of shame complex I'm choosing not to analyze. haha 
> 
> Enjoy :)  
> Thanks so much everyone for the kudos and comments and bookmarks. Makes me feel all tinlgy inside.

Castiel was nowhere in sight when Dean got to the library for their study session the next day. He settled in at their designated station, eyes nervously darting around the room. Ten minutes later, Cas still hadn’t arrived, and Dean started to panic a little bit. What if something bad had happened? Did Castiel forget about him? Maybe he was playing a game this whole time, and now that he’d got Dean’s mouth around his dick, he was done and off to the next conquest. 

A ‘ding’ pulled Dean out of his self-deprecating stupor. _1 New Message from Cas_

Okay, so he hadn’t completely forgotten about Dean. He tapped on the familiar flashing envelope icon.

_Sorry I didn’t contact sooner. Can’t make it. Find me online, I’ll make it up to you._

_Ten minutes._

_I’ll be waiting for you_

Dean scrambled to his feet, he could deal with a disappointing grade in class the next day if it meant he’d have the chance to watch Castiel pleasure himself. The weirdness of Cas’ _job_ hadn’t completely disappeared, but it was becoming less and less unsettling.

He made it back to his room in record time, panting and dizzy as he situated himself in bed with his laptop. Dean opened up the familiar website, clicking on his profile to access the channels he was subscribed to. There was Castiel. Waiting for the live stream to load, Dean got up to lock the door.

After a few moments of staring at the blank black screen, the wait was over. There was Castiel, propped up on his elbows, a look of faux-innocence on his face as he stared wide eyed into the camera. Dean preemptively shucked his pants and underwear, throwing them across the room. He leaned over to retrieve a bottle of lube from the bottom drawer of his desk, not breaking eye contact with the laptop’s screen.

“Hello there.” Castiel’s low rumble of a voice brought Dean’s cock twitching to attention. He leaned back against the head board, taking his half-hard member into hand, steadily jerking on it til he was fully hard. 

Castiel mirrored Dean’s movements, leaning against the wall beside his bed, skipping the teasing and hastily lowering the waistband of his jeans to his ankles. He rubbed at the bulge beneath his boxer briefs, small sighs punctuating each drag of his fingers. He paused for a moment, leaning over to pick up his cellphone. Cas typed up something on his phone and threw it back across the bed, where it landed with a bounce on top of the sheet. 

“Not very professional, Cas.” Dean teased, though Castiel couldn’t hear him. His phone chimed from beside his bed. He snatched it, nearly dropping it as he clicked the envelope with a shaky hand. It was Castiel.

_This one’s for you._

Dean swallowed, focus shifted back to the screen, where Castiel was currently stroking along the prominent line of his erection through his boxer briefs. Cas continued to touch himself through the fabric, biting at his bottom lip as he glanced toward the camera with a flush of embarrassment creeping across his cheeks. A dark spot began to form through the gray fabric as his cock began spurt out precum. Dean stroked himself, swiping a thumb over the place where a bead of his own precum had formed, slicking himself up. He jerked his hand up and down his sensitive shaft, heavy breaths coming in time with Castiel’s. As the moments passed, Castiel’s breaths quickened with his strokes, overstimulated by the friction of the fabric between his palm and his cock. Dean knew what it felt like, remembered the sensation of warm wet fabric on his erection, how impossible self control had been to retain. 

“Oh--” Castiel’s body began to visibly tense up. He leaned his head back against the wall, a salacious rumbling moan rising from somewhere deep inside of him. Dean suddenly understood what was happening. He was making up for the embarrassment he had put Dean through that first time. The conflicting sensations of arousal and guilt as he counterintuitively-

“O-oh my god!” Castiel quickly propped himself up on his knees, anchoring himself to the bed with an outstretched arm behind him, bringing his needy cock into full view. He continued rubbing furiously, undecipherable whispers and breathy moans spilling out of him. 

Fuck. Dean quickened the pace of his strokes, dribbling lube out of the bottle straight on to his cock, sliding in and out of his fist- grip loose and sloppy. He was so close, the telltale warmth and anticipatory coil of release torturing him. This was a lot hotter from his perspective, watching Castiel squirm and moan, knowing how wrong it felt to finish beneath the layer of constricting cotton.

“UNNH” Castiel was about to lose it. Dean watched on, transfixed, as Castiel shuddered, hips stuttering for a moment before he let loose and began to fill his boxer briefs with cum. He soaked through the cotton, wet spot spreading as he worked himself through his release, mouth falling open in ecstasy, grunting in time with the twitch of his cock as he milked out the last of his load. He stayed frozen in that position, eyes clamped shut, breaths coming heavy as he whimpered. “Fuck.. Dean..”

At the sound of his name, Dean lost control, his orgasm almost surprising him, painting his shirt with ribbons of white. His body trembled with the force of his release. When he steadied himself enough to focus his attention back to the screen, he saw Castiel sitting on the bed, holding his knees to his chest, cheeks burning bright red, embarrassment and shame written clear across his face. He sat there for a moment, soaking in his own cum, which was dripping down one of his legs, sticky and wet. On screen, he leaned over to grab his phone, giving a clearer look of the mess he made of himself. He sat back up, leaning over toward the screen and shutting off the live stream.

Dean picked up his phone, beating him to it. 

_Fuck, Cas._

_I see why that made you so uncomfortable_


End file.
